Written by David Coggins

There’s a time for a dress shirt, and hopefully we all know what that is now. My shorthand is that it looks best with a tie. Then there are the sport shirts, which communicate a sign of relaxation. Sport shirts have been known to cause some men anxiety, feeling that they needlessly complicate our sartorial lives. It’s a reminder that it can be hard to relax!

A sport shirt, for this conversation, has a few defining characteristics: It has more pattern and less structure than a dress shirt, and usually a more playful sense of color. We are leaving the realm of stiff collars and pinstripes and entering the world of gingham, dots and even paisley.

So what are we to do in this brave new weekend world? My feeling about daring pattern is that it’s a lot less daring if it’s under a sport coat. Feel nervous about a color or a pattern? Then tame it under a blue blazer. It’s like pouring tonic over a shot of gin, which is too strong when taken neat. Some patterns are just too hot on their own but perfect in small amounts.

That’s a good solution for men who are relaxation averse. If your idea of relaxing is wearing loafers without socks, then I salute you! It’s important to know your nature. You don’t ever want to try too hard to look relaxed. Know your nature and embrace it. But a sport shirt is a good place to start.

For those who are dying to get into the sport shirt game, start with a color that is at one remove from your comfort zone. Pale purple can be your friend. And if you’re ready to wear white jeans, then try them together. I’m not there yet myself, but I have plenty of friends who are, and they look great with a patterned shirt.

Once you get used to the world of pattern, I suspect you will go deeper still. That’s why people become obsessed with madras, even those who were initially afraid of it. It’s like drinking a cocktail with a paper umbrella in it—when the conditions are right, then let the festive mood carry the day!